Synthesis and Anti-tumor Activities of Novel 18β-Glycyrrhetinic Acid Derivatives Attaching Dithiocarbamate Units

doi:10.6023/A1111051

Acta Chimica Sinica ›› 2012, Vol. 70 ›› Issue (07): 852-858 .DOI: 10.6023/A1111051 Previous Articles Next Articles

Full Papers

新型18β-甘草次酸氨基二硫代甲酸酯衍生物的合成及抗癌活性研究

陈凑喜^a, 李学强^a,b, 李天才^a, 周学章^c

a 宁夏大学化学化工学院银川 750021;
b 宁夏天然药物工程技术研究中心银川 750021;
c 宁夏大学西部特色生物资源保护与利用教育部重点实验室银川 750021

投稿日期:2011-11-05 修回日期:2012-01-31 发布日期:2012-02-14
通讯作者: 李学强 E-mail:lixq@nxu.edu.cn
基金资助:
国家自然科学基金(No. 21062014)、教育部科学技术研究重点项目(No. 210237)、宁夏自然科学基金(No. NZ0606)和云南大学自然资源药物化学教育部重点实验室开放基金(No. 200902205)资助项目.

Synthesis and Anti-tumor Activities of Novel 18β-Glycyrrhetinic Acid Derivatives Attaching Dithiocarbamate Units

Chen Couxi^a, Li Xueqiang^a,b, Li Tiancai^a, Zhou Xuezhang^c

a School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021;
b Ningxia Development Center of Natural Products and Medication, Yinchuan 750021;
c Key Laboratory of Ministry of Education for Protection and Utilization of Special Biological Resources in Western China, Ningxia University, Yinchuan 750021

Received:2011-11-05 Revised:2012-01-31 Published:2012-02-14
Supported by:
Project supported by National Natural Science Foundation of China (No. 21062014), Key Project of Chinese Ministry of Education (No. 210237), Natural Science Foundation of Ningxia Province of China (No. NZ0606) and Key Laboratory of Medicinal Chemistry for Natural Resource, Yunnan University (No. 200902205) for financial support.

Ten new 18β-glycyrrhetinic acid derivatives with dithiocarbamate units were prepared by amidation of 18β-glycyrrhetinic acid and piperazine followed with one-pot condensation of the amide, CS₂ and alkyl halides in the presence of potassium carbonate in CHCl₃. The structures of all the new compounds were identified by NMR spectra, IR and HRMS technology. Anti-tumor activities of the 18β-glycyrrhetinic acid derivatives against human hepatoma SMMC-7721 cell lines were evaluated by 3-(4,5-dimethylthiazol- 2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. They were found to inhibit the liver cancer cell proliferation and induce apoptosis as the lowest IC₅₀ value was only 14.42 μg/mL.

Key words: 18β-glycyrrhetinic acid, dithiocarbamates, synthesis, anti-tumor activity

Cite this article

Chen Couxi, Li Xueqiang, Li Tiancai, Zhou Xuezhang. Synthesis and Anti-tumor Activities of Novel 18β-Glycyrrhetinic Acid Derivatives Attaching Dithiocarbamate Units[J]. Acta Chimica Sinica, 2012, 70(07): 852-858 .

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

1 Kao, T.-C.; Shyu, M.-H.; Yen, G.-C. J. Agric. Food Chem.2010, 58, 8623.

2 Wang, C.-Y.; Kao, T.-C.; Lo, W.-H.; Yen, G.-C. J. Agric. Food Chem. 2011, 59, 7726.

3 Maitraie, D.; Hung, C.-F.; Tu, H.-Y.; Liou, Y.-T.; Wei, B.-L.; Yang, S.-C.; Wang, J.-P.; Lin, C.-N. Bioorg. Med. Chem.2009, 17, 2785.

4 Subba-Rao, G. S. R.; Kondaiah, P.; Singh, S. K.; Ravanan, P.; Sporn, M. B. Tetrahedron 2008, 64, 11541.

5 Um, S.-J.; Park, M.-S.; Park, S.-H.; Han, H.-S.; Kwon, Y.-J.; Sin, H.-S. Bioorg. Med. Chem. 2003, 11, 5345.

6 Kao, T.-C.; Shyu, M.-H.; Yen, G.-C. J. Agric. Food Chem.2009, 57, 754.

7 Dehpour, A. R.; Zolfaghari, M. E.; Samadian, T.; Kobarfard, F.; Faizi, M.; Assari, M. Int. J. Pharm. 1995, 119, 133.

8 Moro, T.; Shimoyama, Y.; Kushida, M.; Hong, Y. Y.; Nakao, S.; Higashiyama, R.; Sugioka, Y.; Inoue, H.; Okazaki, I.; Inagaki, Y. Life Sci. 2008, 83, 531.

9 Lu, J.-R.; Hu, J.; Yang, S.; Yong, J. Org. Lett. 2011, 13,3372.

10 Curreli, F.; Friedman-Kien, E. A.; Flore, O. J. Clin. Invest.2005, 115, 642.

11 Vodovozova, E. L.; Kuznetsova, N. R.; Gaenko, G. P.; Molotkovsky, J. G. Russ. J. Bioorg. Chem. 2007, 33, 436.

12 Zhao, X.-J.; Fan, Y.-P.; Wang, D.-Y.; Hu, Y.-L.; Guo, L.-W.; Ruan, S.-L.; Zhang, J.; Yuan, J. Vaccine 2011, 29, 9611.

13 Lallemand, B.; Chaix, F.; Bury, M.; Bruyère, C.; Ghostin, J.; Becker, J.-P.; Delporte, C.; Gelbcke, M.; Mathieu, V.; Dubois, J.; Prévost, M.; Jabin, I.; Kiss, R. J. Med. Chem. 2011,54, 6501.

14 Csuk, R.; Schwarz, S.; Siewert, B.; Kluge, R.; Str?hl, D.; Eur. J. Med. Chem. 2011, 46, 5356.

15 Liu, D.; Song, D.; Guo, G.; Wang, R.; Lv, J.-L.; Jing, Y.-K.; Zhao, L.-X. Bioorg. Med. Chem. 2007, 15, 5432.

16 Amra, A. E.-G. E.; Ali, K. A.; Abdalla, M. M. Eur. J. Med. Chem. 2009, 44, 901.

17 René, C.; Stefan, S.; Ralph, K.; Csuk, R.; Schwarz, S.; Kluge, R.; Str?hl, D. Eur. J. Med. Chem. 2010, 45, 5718.

18 Nieuwenhuizen, P. J.; Ehlers, A. W.; Haasnoot, J. G.; Janse, S. R.; Reedijk, J.; Baerends, E. J. J. Am. Chem. Soc. 1999,121, 163.

19 Richard, W. H. Lubr. Eng. 2000, 56, 45.

20 Rhenals, M. V.; Strasberg-Rieber, M.; Rieber, M. J. Med. Chem. 2010, 53, 1627

21 Ronconi, L.; Marzano, C.; Zanello, P.; Corsini, M.; Miolo, G.; Maccà, C.; Trevisan, A.; Fregona, D. J. Med. Chem.2006, 49, 1648.

22 Caldas, E. D.; Hosana Concei??o, M.; Miranda, M. C. C.; de Souza, L. K. R.; Lima, J. F. J. Agric. Food Chem. 2001,49, 4521.

23 Cheng, A.-C.; Huang, T.-C.; Lai, C.-S.; Kuo, J.-M.; Huang, Y.-T.; Lo, C.-Y.; Ho, C.-T.; Pan, M.-H. J. Agric. Food Chem. 2006, 54, 4215.

24 Sharma, S.; Rashid, F.; Bano, B. J. Agric. Food Chem.2005, 53, 6027.

25 Horita, Y.; Takii, T.; Kuroishi, R.; Chiba, T.; Ogawa, K.; Kremer, L.; Sato, Y.; Lee, Y. S.; Hasegawa, T.; Onozaki, K. Bioorg. Med. Chem. Lett. 2011, 21, 899.

26 Wang, X.-J.; Xu, H.-W.; Guo, L.-L.; Zheng, J.-X.; Xu, B.; Guo, X.; Zheng, C.-X.; Liu, H.-M. Bioorg. Med. Chem. Lett. 2011, 21, 3074.

27 Pedras, M. S. C.; Minic, Z.; Hossain, S. Bioorg. Med. Chem.2012, 20, 225.

28 Gao, D.; Scholz, F.; Nothofer, H.-G.; Ford, W. E.; Scherf, U.; Wessels, J. M.; Yasuda, A.; Wrochem, F. V. J. Am. Chem. Soc. 2011, 133, 5921.

29 Fox, O. D.; Cookson, J.; Wilkinson, E. J. S.; Drew, M. G. B.; MacLean, E. J.; Teat, S. J.; Beer, P. D. J. Am. Chem. Soc. 2006, 128, 6990.

30 Wei, M.-X.; Feng, L.; Li, X.-Q.; Zhou, X.-Z.; Shao, Z.-H. Eur. J. Med. Chem. 2009, 44, 3340.

31 Azizi, N.; Aryanasab, F.; Saidi, M. R. Org. Lett. 2006, 8,5275.

32 Li, R.-T.; Ge, Z.-M.; Cheng, T.-M.; Cai, M.-S. Chem. J. Chin. Univ. 1999, 20, 1897 (in Chinese). (李润涛, 葛泽梅, 程铁明, 蔡孟深, 高等学校化学学报,1999, 20, 1897.)

33 Feng, W.-Y.; He, B.; Zhou, L.-M. Chin. Tradit. Pat. Med.2010, 32, 189 (in Chinese). (冯文宇, 何兵, 周黎明, 中成药, 2010, 32, 189.)

[1]	Lingyue Yang, Yunting Li, Chao Shu. Research Progress on Sultine [J]. Acta Chimica Sinica, 2024, 82(2): 171-189.
[2]	Yi Wan, Jianghua He, Yuetao Zhang. Research Progress in Precision Polymerization of Polar Olefin Monomers by Lewis Pairs^★ [J]. Acta Chimica Sinica, 2023, 81(9): 1215-1230.
[3]	Mei Hong, Jinqiang Gao, Tong Li, Shihe Yang. In-situ Etching Strategy for Manipulation of Hierarchical Zeolite and Its Application^★ [J]. Acta Chimica Sinica, 2023, 81(8): 937-948.
[4]	Shaoyan Gan, Shengyu Zhong, Liting Wang, Lei Shi. Synthesis and Application of Organic Hypervalent Bromine Reagents [J]. Acta Chimica Sinica, 2023, 81(8): 1030-1042.
[5]	Wenshan Zheng, Guanbin Gao, Hao Deng, Taolei Sun. Room Temperature Synthesis and Near-infrared Fluorescence Performance Optimization of Ag₂Se@Ag₂S Core-shell Quantum Dots [J]. Acta Chimica Sinica, 2023, 81(7): 763-770.
[6]	Yandong Zhang, Shoufei Zhu. Perspective for Phosphine Ligands with Cyclopropane Backbone^★ [J]. Acta Chimica Sinica, 2023, 81(7): 777-783.
[7]	Li Liu, Gang Zheng, Guoqiang Fan, Hongguang Du, Jiajing Tan. Research Progress in Organic Reactions Involving 4-Acyl/Carbamoyl/Alkoxycarbonyl Substituted Hantzsch Esters [J]. Acta Chimica Sinica, 2023, 81(6): 657-668.
[8]	Kanbinuer Nuermaimaiti, Chao Wang, Shiwei Luo, Abudu Rexit Abulikemu. Research on Selective Dehalogenation of α,α,α-Trihalogen (Chloro, Bromo) methyl Ketones Under Electrochemical Conditions [J]. Acta Chimica Sinica, 2023, 81(6): 582-587.
[9]	Wang Jun, Xu Xiaomei, Zhou Jiaolong, Zhao Yanan, Sun Xiuli, Tang Yong, He Sufang, Yang Hongmei. Synthesis of New Sulfur-free and Phosphorus-free Ether-ester and Study on Its Properties As Ashless Friction Modifier [J]. Acta Chimica Sinica, 2023, 81(5): 461-468.
[10]	Junchang Chen, Mingxing Zhang, Shuao Wang. Research Progress of Synthesis Methods for Crystalline Porous Materials [J]. Acta Chimica Sinica, 2023, 81(2): 146-157.
[11]	Yang Gao, Xuexin Zhang, Jinsheng Yu, Jian Zhou. Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1590-1608.
[12]	Zhiping Chen, Yongle Meng, Jing Lu, Wenwu Zhou, Zhiyuan Yang, Anning Zhou. Preparation of Fe@Si/S-34 Catalysts and Its Catalytic Performance for Syngas to Olefins [J]. Acta Chimica Sinica, 2023, 81(1): 14-19.
[13]	Xiaochen Wang, Zeyao Ji, Jian Liu, Bingfu Wang, Hui Jin, Lixin Zhang. Advances in Organocatalytic Asymmetric Reactions Involving Thioesters [J]. Acta Chimica Sinica, 2023, 81(1): 64-83.
[14]	Hongdan Zhang, Xinyu Lan, Peng Cheng. Advances in Hydroxyl Free Radical Assisted Synthesis of Zeolite [J]. Acta Chimica Sinica, 2023, 81(1): 100-110.
[15]	Xia Liu, Chunxiang Kuang, Changhui Su. Transition-metal Catalyzed 1,2,3-Triazole-assisted C—H Functionalization Processes [J]. Acta Chimica Sinica, 2022, 80(8): 1135-1151.

新型18β-甘草次酸氨基二硫代甲酸酯衍生物的合成及抗癌活性研究

Synthesis and Anti-tumor Activities of Novel 18β-Glycyrrhetinic Acid Derivatives Attaching Dithiocarbamate Units

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments